Attempts to get Ukraine to carry out investigations
Since at least May 2019, Giuliani urged Ukraine's president, Volodymyr Zelenskyy, to investigate oil company Burisma, whose board once included Joe Biden's son Hunter Biden, and check for irregularities in Ukraine's investigation of Paul Manafort. He said such investigations would benefit his client's defense, and that his efforts had Trump's support. Toward this end, Giuliani met with Ukrainian officials throughout 2019. In July 2019, BuzzFeed News reported that Soviet-born Americans, and Igor Fruman and Lev Parnas, were liaisons between Giuliani and Ukrainian government officials in this effort. Parnas and Fruman, prolific Republican donors, neither registered as foreign agents in the United States nor were approved by the State Department. Giuliani responded that the report was "a pathetic effort to cover up what are enormous allegations of criminality by the Biden family". By September 2019, there had been no evidence of wrongdoing by the Bidens.
In October 2019, Giuliani hired former Watergate prosecutor Jon Sale to represent him in the House Intelligence Committee's impeachment investigation. The committee issued a subpoena to Giuliani asking him to release documents related to the Ukraine scandal. The New York Times reported on October 11, 2019, that the U.S. Attorney for the Southern District of New York, was investigating him for violating lobbying laws related to his activities in Ukraine. Bloomberg News reported that the investigation could extend to bribery of foreign officials or conspiracy, and The Wall Street Journal reported Giuliani was being investigated for a possible profit motive in a Ukrainian gas venture. Giuliani denied having any interest in the venture. Federal prosecutors issued subpoenas to associates of Giuliani to investigate individuals, apparently including Giuliani, on potential charges, including money laundering, obstruction of justice, conspiracy to defraud the US, and mail/wire fraud.
Giuliani was paid $500,000 to consult for Parnas' company named "Fraud Guarantee". Trump supporter attorney Charles Gucciardo paid Giuliani on behalf of Fraud Guarantee in two $250,000 payments, in 2018. In May 2019, Giuliani described Ukraine's chief prosecutor Yuriy Lutsenko as a "much more honest guy" than his predecessor, Viktor Shokin. After Lutsenko was removed from office, he said in September 2019 that he found no evidence of wrongdoing by the Bidens, and had met Giuliani about ten times. Giuliani reversed his stance, saying that Shokin is the one people "should have spoken to", while Lutsenko acted "corruptly" and "is exactly the prosecutor that Joe Biden put in in order to tank the case".
In September 2019, as reports surfaced that a whistleblower was alleging high-level misconduct related to Ukraine, Giuliani went on CNN. When asked if he had tried to get Ukrainian officials to investigate Biden, he replied "No, actually I didn't", but thirty seconds later said, "Of course I did". In a tweet, he seemed to confirm reports Trump had withheld military assistance scheduled for Ukraine unless they carried out the investigation. He said, "The reality is that the president of the United States, whoever he is, has every right to tell the president of another country you better straighten out the corruption in your country if you want me to give you a lot of money. If you're so damn corrupt that you can't investigate allegations – our money is going to get squandered." Tom Bossert, a former Homeland Security Advisor in the Trump administration, described Giuliani's theory that Ukraine was involved in 2016 U.S. election interference as "debunked"; Giuliani responded that Bossert "doesn't know what the hell he's talking about".
On October 2, 2019, Steve Linick, the State Department's inspector general, delivered a packet of apparent disinformation regarding President Biden and former ambassador to Ukraine, Marie Yovanovitch, to Capitol Hill. Linick told congressional aides his office questioned Ulrich Brechbuhl, Mike Pompeo's advisor about the origins of the packet. Giuliani acknowledged he passed the packet to Pompeo. In a November 2019 interview, he confirmed he had "needed Yovanovitch out of the way" because she was going to make his investigations difficult. Giuliani added, "They (the State Department) told me they would investigate it." Giuliani persuaded Trump to remove Yovanovitch from office in spring 2019. By April 2021, the U.S. attorney's office in Manhattan was investigating the role of Giuliani in Yovanovitch's removal.
U.S. ambassador to the European Union Gordon Sondland testified that Trump delegated policy on Ukraine to Giuliani. The late 2019 impeachment inquiry into Donald Trump centered around Giuliani's actions involving Ukraine. In testimony and reports of the House Intelligence Committee, Giuliani's name was mentioned more than any but Trump's. Experts suggested Giuliani may have violated the Logan Act. On November 22, 2019, Giuliani sent a letter to Senator Lindsey Graham, chairman of the Committee on the Judiciary, informing him of three witnesses from Ukraine who Giuliani said had direct evidence of Democratic criminal conspiracy with Ukrainians to prevent Trump's election and, after his election, to remove him via contrived charges. Giuliani claimed the witnesses had evidence of the Biden family's involvement in bribery, money laundering and Hobbs Act extortion. The letter sought Graham's help obtaining visas for the witnesses to testify. Graham invited Giuliani to share his findings with the Judiciary Committee, and advised him "to share what he got from Ukraine with the [intelligence community] to make sure it's not Russia propaganda".
Dmytro Firtash is a Ukrainian oligarch prominent in natural gas. In 2017, the Justice Department characterized him as in the "upper echelon of Russian organized crime". Since his 2014 arrest in Vienna, at the request of American authorities, he has been living there on $155 million bail fighting extradition to the US on bribery and racketeering charges. Firtash's attorneys obtained a September 2019 statement from Viktor Shokin, the former Ukrainian prosecutor who was forced out under pressure from multiple countries and non-governmental organizations, as conveyed to Ukraine by Joe Biden. Shokin falsely asserted that Biden had him fired because he refused to stop his investigation into Burisma. Giuliani, who asserts he has "nothing to do with" and has "never met or talked to" Firtash, promoted the statement in television appearances as purported evidence of wrongdoing by the Bidens. Giuliani told CNN he met with a Firtash attorney at the time he was seeking information about the Bidens. Firtash was represented by Trump and Giuliani associates Joseph diGenova and his wife Victoria Toensing, having hired them on Parnas' recommendation in July 2019.
The New York Times reported that Giuliani had directed Parnas to approach Firtash with the recommendation, with the proposition that Firtash could help provide damaging information on Biden, which Parnas' attorney described was "part of any potential resolution to [Firtash's] extradition matter". Shokin's statement notes that it was prepared "at the request of lawyers acting for Dmitry Firtash ('DF'), for use in legal proceedings in Austria". Bloomberg News reported that during summer 2019 Firtash associates began attempting to dig up dirt on the Bidens to solicit Giuliani's assistance with Firtash's legal matters; it also reported that Giuliani's publicizing of the Shokin statement had reduced the chances of the Justice Department dropping the charges against Firtash, as it would appear to be a political quid pro quo. The Washington Post reported on October 22 that after they began representing Firtash, Toensing and diGenova secured a rare face-to-face meeting with U.S. Attorney General Bill Barr to argue the Firtash charges should be dropped, but he declined to intervene.
On October 18, The New York Times reported that weeks earlier, before his associates Parnas and Fruman were indicted, Giuliani met with officials with the criminal and fraud divisions of the Justice Department regarding what Giuliani characterized as a "very sensitive" foreign bribery case involving a client of his. The Times did not name whom the case involved, but after publication of the story Giuliani told a reporter it was not Firtash. The Justice Department said its officials would not have met with Giuliani had they known his associates were under investigation by the U.S. Attorney for the Southern District of New York.
On December 3, 2019, the House Intelligence Committee's report included phone records, including calls made by Giuliani between April and August 2019. Calls involved Giuliani in contact with Kurt Volker, Republican representative and House Intelligence Committee ranking member Devin Nunes, Parnas, the White House switchboard, and an unidentified White House official whose phone number is referenced as "-1". Chairman Adam Schiff of the committee announced after the report's release that the committee was investigating whether "-1" referred to President Trump, citing grand jury evidence from the trial of Trump-associate Roger Stone in which phone number "-1" referred to Trump. Analyst Philip Bump reasoned that Giuliani's calls with "-1" are 'likely' calls with Trump citing that Giuliani spoke longer with "-1" than anyone else, "-1" always calls Giuliani, and generally after Giuliani calls the White House switchboard, and timing of Trump actions after Giuliani's calls with "-1" ended.
In December 2019, while the House Judiciary Committee began hearings for the impeachment inquiry, Giuliani returned to Ukraine to interview former officials for a documentary seeking to discredit impeachment proceedings. U.S. officials told The Washington Post that Giuliani would have been a target of Russian intelligence efforts during Trump's presidency, and particularly after Giuliani turned his focus to Ukraine – a former Soviet republic under attack from Russia and with deep penetration by Russian intelligence. Analysts say Trump and Giuliani's habit of communicating over unencrypted lines makes it likely foreign agencies would be listening, and agencies often collect intelligence through monitoring communications of people who interact with their target.
NBC News reported in December 2020 that SDNY investigators, had discussed with Justice Department officials the possibility of acquiring Giuliani's emails, which might require headquarters approval due to protection by attorney–client privilege. The New York Times reported in 2021 that the SDNY had requested a search warrant of Giuliani's electronic records in summer 2020, but were met with resistance from political appointees in the Washington headquarters, ostensibly because the election was near, while career officials were supportive. The Justice Department generally avoids taking significant actions relating to political figures that might become public within sixty days of an election. Political appointees nevertheless opposed the effort after the election, noting Giuliani played a leading role in challenging the election results. The officials deferred the matter to the incoming Biden administration.
Federal investigators in Manhattan executed search warrants on April 28, 2021, at Giuliani's office and Upper East Side apartment, seizing his electronic devices. In April 2021, Giuliani's attorney said investigators told him they had searched his client's iCloud account beginning in late 2019, later arguing to a judge that the search was illegal and so the raid on Giuliani's properties was "fruit of this poisoned tree", demanding to review documents justifying the iCloud search. In May 2021, the SDNY confirmed that in late 2019 it obtained search warrants for Giuliani's iCloud account, as part of "an ongoing, multi-year grand jury investigation into conduct involving Giuliani, Toensing, and others", and argued that attorneys for Giuliani were not entitled to review the underlying documents of the warrants prior to any charges. Giuliani and Toensing asserted their attorney-client privilege may have been violated by the iCloud searches, which investigators disputed, saying they employed a "filter team" to prevent them from seeing information protected by privilege. Federal judge J. Paul Oetken ruled in favor of investigators and granted their request for a special master to ensure attorney-client privilege was maintained. The special master released more than 3,000 of Giuliani's communications to prosecutors in 2022, agreeing to withhold forty for which Giuliani had asserted "privilege and/or highly personal" status and rejecting 37 such assertions.
The New York Times reported in 2021 that the SDNY was scrutinizing Giuliani's association with Firtash in efforts to discredit the Bidens, and efforts to lobby the Trump administration on behalf of Ukrainian officials and oligarchs. Time reported it had spoken with three unidentified witnesses who said they were questioned by investigators, two of whom said they had worked with Giuliani while cooperating with investigators; one said investigators were particularly interested in Giuliani's association with Firtash.
U.S. intelligence community analysis released in 2021 found Ukrainian politician Andrii Derkach was among proxies of Russian intelligence who promoted and laundered misleading or unsubstantiated narratives about Biden "to US media organizations, US officials, and prominent US individuals, including some close to former President Trump and his administration". Giuliani met with Derkach in December 2019. The New York Times confirmed in May 2021 that Derkach was the subject of a criminal investigation into foreign interference in the 2020 election, and further reported that "Federal prosecutors in Brooklyn have been investigating whether several Ukrainian officials helped orchestrate a wide-ranging plan to meddle in the 2020 presidential campaign, including using Rudolph W. Giuliani to spread their misleading claims about President Biden and tilt the election in Donald J. Trump's favor." On June 8, 2021, CNN uncovered audio of a 2019 call, stating that "Giuliani relentlessly pressured and coaxed the Ukrainian government to investigate baseless conspiracies about then-candidate Joe Biden." In November 2022, SDNY stated they would not indict Giuliani for his activities in Ukraine.